Dimethylformamide → HCID 135887174, compound

HRID 2195743Notes

Reaction equation

[CH:1]1([C@H:7]([NH:12][C:13]([C:15]2[O:16][C:17]([C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([NH2:27])[CH:21]=3)=[CH:18][CH:19]=2)=[O:14])[C:8](=[O:11])[NH:9][CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:28][N:29]1[CH:33]=[C:32](C=O)[C:31]([CH3:36])=[N:30]1.S(=O)(O)[O-].[Na+].[CH3:42]N(C=O)C>>[CH:1]1([C@H:7]([NH:12][C:13]([C:15]2[O:16][C:17]([C:20]3[CH:25]=[CH:24][C:23]4[N:26]=[C:42]([C:33]5[N:29]([CH3:28])[N:30]=[C:31]([CH3:36])[CH:32]=5)[NH:27][C:22]=4[CH:21]=3)=[CH:18][CH:19]=2)=[O:14])[C:8](=[O:11])[NH:9][CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 8472851,3-dimethyl-1H-pyrazole-4-carbaldehyde

HCID 23665763Sodium Bisulfite

HCID 46207050HCID 46207050, compound

Product 1

HCID 135887174HCID 135887174, compound

Conditions

Temperature: 130 °C

Procedure

5-(3,4-Diamino-phenyl)-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide (25 mg, 67 mmol), 1,3-dimethyl-1H-pyrazole-4-carbaldehyde (9.2 mg, 74 mmol), and sodium bisulfite (7.73 mg, 74 mmol) are dissolved in DMF (1 mL) and the mixture is heated at 130° C. for 12 h. The mixture is filtered and purified on reversed phase (HPLC). The product is obtained as a beige solid. 4.2 mg, 13%, LC/MS ESI m/z (M+H)+=476.54.

Workup

filtrationThe mixture is filtered
custompurified on reversed phase (HPLC)
customThe product is obtained as a beige solid

Sources & evidence

ORD record: ord-d8e84978c2e8426b8161b9484883825d
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338367B2

Reaction notes

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